This invention relates to ortho-heterocyclic sulfonylureas and in particular, to their use as agricultural chemicals such as herbicides and growth regulants.
U.S. Pat. No. 4,127,405 teaches compounds which are useful for controlling weeds in wheat having the formula: ##STR1## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA0 R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA0 R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atom; PA0 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA0 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA0 W and Q are independently oxygen or sulfur; PA0 n is 0, 1 or 2; PA0 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and PA0 Y is methyl or methoxy; or their agriculturally suitable salts; provided that: PA0 R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA0 R is H or C.sub.1 -C.sub.4 alkyl; PA0 R.sub.1 is H, F, Cl, Br, CH.sub.3, CF.sub.3 or OCH.sub.3 ; PA0 R.sub.2 is H, CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, Cl or Br; PA0 R.sub.3 is H, CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, Cl or Br; PA0 R.sub.5 is H, CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, Cl or Br; PA0 R.sub.6 is H, CH.sub.3 or C.sub.2 H.sub.5 ; PA0 R.sub.8 is H, CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, Cl or Br; PA0 R.sub.9 is H, CH.sub.3 or C.sub.2 H.sub.5 ; PA0 R.sub.4, R.sub.7, R.sub.10 and R.sub.11 are independently H or C.sub.1 -C.sub.4 alkyl; PA0 R.sub.12 is H or CH.sub.3 ; PA0 R.sub.13 is H or CH.sub.3 ; PA0 R.sub.14 is H, CH.sub.3, C.sub.2 H.sub.5, Cl, Br, CH.sub.3 O, C.sub.2 H.sub.5 O or CH.sub.3 S; PA0 R.sub.15 is H, CH.sub.3 or C.sub.2 H.sub.5 ; PA0 R.sub.16 is H, CH.sub.3 or C.sub.2 H.sub.5 ; PA0 A is ##STR10## X is CH.sub.3, OCH.sub.3 or Cl; Y is CH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH(OCH.sub.3).sub.2, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, OCH.sub.2 CH.sub.2 OCH.sub.3, OCH.sub.2 CF.sub.3, CF.sub.3, SCH.sub.3 or ##STR11## Z is CH or N; X.sub.1 is CH.sub.3, OCH.sub.3 or Cl; PA0 G is O or CH.sub.2 ; PA0 X.sub.2 is C.sub.1 -C.sub.3 alkyl or CH.sub.2 CF.sub.3 ; PA0 Y.sub.2 is CH.sub.3 O, C.sub.2 H.sub.5 O, CH.sub.3 S or C.sub.2 H.sub.5 S; PA0 (a) when R.sub.8 is other than H, CH.sub.3, C.sub.2 H.sub.5 or CH.sub.3 S, then W is S or O; PA0 (b) the total number of carbon atoms of R.sub.4, R.sub.7, R.sub.10 and R.sub.11 is less than or equal to 4; PA0 (c) when X is Cl, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA0 (d) when Q is ##STR12## then R.sub.13 is H, R is other than H, X is Cl or OCH.sub.3 and Y is OCH.sub.3 or OC.sub.2 H.sub.5 ; and PA0 (e) when W" is S, then R.sub.13 is H; PA0 (1) Compounds of Formula I where PA0 (2) Compounds of the Preferred 1 where R.sub.1 and R.sub.13 are H; PA0 (3) Compounds of Preferred (2) where PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(1-methyl-1H-imidazol-2-yl )benzenesulfonamide; PA0 N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(1-methyl-1H-imidazol-2-yl) benzenesulfonamide; PA0 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(1-methyl-1H-imidazol -2-yl)benzenesulfonamide; PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(oxazol-2-yl)benzenesulfon amide; PA0 N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(oxazol-2-yl)benzenesulfona mide; PA0 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(oxazol-2-yl)benzenes ulfonamide; PA0 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(oxazol-2-yl)benzenes ulfonamide; PA0 N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(oxazol-2-yl)benzenesu lfonamide; PA0 N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(oxazol-2-yl)ben zenesulfonamide; and PA0 2-(4,5-dihydro-5,5-dimethyloxazol-2-yl)-N-[(4,6-dimethoxy-1,3,5-triazin-2-y l)aminocarbonyl]benzenesulfonamide. PA0 R.sub.6 is CH.sub.3, CH.sub.3 CH.sub.2. PA0 R.sub.9 is CH.sub.3 or CH.sub.3 CH.sub.2. PA0 R.sub.3 is CH.sub.3, CH.sub.3 CH.sub.2, CH.sub.3 O or CH.sub.3 CH.sub.2 O. PA0 (1) J. V. Metzger (ed.), Chem. Heterocyclic Compounds, 34, parts (1-3) (1978-1979). PA0 (2) J. M. Sprague and A. H. Land, "Heterocyclic Compounds", (R. C. Elderfield, ed.) V, 484-722. Wiley, N.Y.
(a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA1 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA1 (c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen. PA1 Q is ##STR13## A is ##STR14## and Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR15## PA1 R is CH.sub.3 or C.sub.2 H.sub.5 ; PA1 R.sub.2, R.sub.3, R.sub.5, R.sub.6, R.sub.8, R.sub.9, R.sub.14, R.sub.15 and R.sub.16 are independently H, CH.sub.3 or C.sub.2 H.sub.5 ; PA1 R.sub.4, R.sub.7, R.sub.10 and R.sub.11 are independently H or CH.sub.3 ; and PA1 W" is O; PA1 Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or ##STR16## and A is ##STR17## (4) Compounds of Preferred (3) where Q is ##STR18## (5) Compounds of Preferred (3) where Q is ##STR19## (6) Compounds of Preferred (3) where Q is ##STR20## (7) Compounds of Preferred (3) where Q is ##STR21## (8) Compounds of Preferred (3) where Q is ##STR22## (9) Compounds of Preferred (3) where Q is ##STR23## (10) Compounds of Preferred (3) where Q is ##STR24## (11) Compounds of Preferred (3) where Q is ##STR25## (12) Compounds of Preferred (3) where Q is ##STR26## (13) Compounds of Preferred (3) where Q is ##STR27## (14) Compounds of Preferred (3) where Q is ##STR28## (15) Compounds of Preferred (3) where Q is ##STR29## (16) Compounds of Preferred (3) where Q is ##STR30## (17) Compounds of Preferred (3) where Q is ##STR31## (18) Compounds of Preferred (3) where Q is ##STR32## and (19) Compounds of Preferred (3) where PA1 Q is ##STR33##
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR2## wherein
R=H, halogen, CF.sub.3 or alkyl.
Logemann et al., Chem. Ab., 53, 18052g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR3## wherein R is butyl, phenyl or ##STR4## and R.sub.1 is hydrogen or methyl.
When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR5## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides, ##STR6## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
Compounds of Formula (ii), and their use as antidiabetic agents, are reported in J. Drug. Res. 6, 123 (1974), ##STR7## wherein R is pyridyl.
European Patent Application No. 7687, discloses herbicidal sulfonylureas which contain an o-carboalkoxybenzene moiety.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, barley, wheat, and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops.